CN113773321B - Organic compound, and electronic component and electronic device using same - Google Patents
Organic compound, and electronic component and electronic device using same Download PDFInfo
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- CN113773321B CN113773321B CN202111095295.1A CN202111095295A CN113773321B CN 113773321 B CN113773321 B CN 113773321B CN 202111095295 A CN202111095295 A CN 202111095295A CN 113773321 B CN113773321 B CN 113773321B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 49
- 125000003118 aryl group Chemical group 0.000 claims abstract description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 132
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 239000010410 layer Substances 0.000 claims description 83
- -1 triphenylsilyl groups Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052805 deuterium Inorganic materials 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 239000002346 layers by function Substances 0.000 claims description 17
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 59
- 239000000463 material Substances 0.000 abstract description 33
- 230000005540 biological transmission Effects 0.000 abstract description 3
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 27
- 239000002994 raw material Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 125000000753 cycloalkyl group Chemical group 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000007858 starting material Substances 0.000 description 15
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 125000001624 naphthyl group Chemical group 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000004665 trialkylsilyl group Chemical group 0.000 description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000004076 pyridyl group Chemical group 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000005561 phenanthryl group Chemical group 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
- 238000000132 electrospray ionisation Methods 0.000 description 6
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- CHFHJZQNRFZRNY-UHFFFAOYSA-N 4-[tert-butyl-(1,1-dichloro-2-methylpropan-2-yl)phosphanyl]-N,N-dimethylaniline Chemical compound ClC(C(C)(C)P(C1=CC=C(C=C1)N(C)C)C(C)(C)C)Cl CHFHJZQNRFZRNY-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- QZTQQBIGSZWRGI-UHFFFAOYSA-N 2-n',7-n'-bis(3-methylphenyl)-2-n',7-n'-diphenyl-9,9'-spirobi[fluorene]-2',7'-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=C3C4(C5=CC=CC=C5C5=CC=CC=C54)C4=CC(=CC=C4C3=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QZTQQBIGSZWRGI-UHFFFAOYSA-N 0.000 description 3
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- LYKXFSYCKWNWEZ-UHFFFAOYSA-N pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile Chemical compound N1=CC=CC2=C(N=C(C(C#N)=N3)C#N)C3=C(C=CC=N3)C3=C21 LYKXFSYCKWNWEZ-UHFFFAOYSA-N 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 101000595182 Homo sapiens Podocan Proteins 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 102100036036 Podocan Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
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- 150000003254 radicals Chemical class 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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Abstract
The application relates to the technical field of organic materials, in particular to an organic compound, which takes an azaphenanthrene ring as a parent nucleus, and introduces an asymmetric aromatic group in conjugated connection on the parent nucleus, so that the dipole moment of the compound is improved, the molecular polarity is improved, and then the electron transmission performance is improved. The compound can be used as a main material of an electron transport layer or an organic light-emitting layer, and can remarkably improve the efficiency and the service life of an organic electroluminescent device.
Description
Technical Field
The present disclosure relates to the field of organic electroluminescence technology, and in particular, to an organic compound, and an electronic element and an electronic device using the same.
Background
An organic light-emitting diode (OLED) is a principle that when an electric field is applied between an anode and a cathode, holes on the anode side and electrons on the cathode side move to a light-emitting layer, and are combined to form excitons on the light-emitting layer, the excitons are in an excited state to release energy outwards, and the process of releasing energy from the excited state to a ground state emits light outwards. Since the report of organic molecular electroluminescence by Kodak corporation in the United states in 1987 and polymer electroluminescence by Cambridge university in the United states in 1990, research and development have been conducted in various countries around the world. The material has the advantages of simple structure, high yield, low cost, active luminescence, high response speed, high fraction and the like, has the performances of low working voltage, full solid state, non-vacuum, anti-oscillation, low temperature resistance (-40 ℃) and the like, is considered to be a new technology most likely to replace a liquid crystal display in the future, and is greatly concerned.
In the existing organic electroluminescent devices, the life and efficiency are the most important problems, and with the large area of the display, the operating voltage is also improved, and the luminous efficiency and the current efficiency are also improved, so that it is necessary to continuously develop a more stable high-performance main material to further improve the performance of the organic electroluminescent device.
Disclosure of Invention
The object of the present application is to provide an organic compound, and an electronic component and an electronic device using the same, which have high luminous efficiency and service life.
In order to achieve the above object, a first aspect of the present disclosure provides an organic compound having a group represented by the following formula 1:
wherein X is 1 、X 2 、X 3 And X 4 Each independently selected from C, C (H) or N, and X 1 、X 2 、X 3 And X 4 One or two of them are N;
R 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroaryl group;
R 2 and R is 3 Are the same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups or groups shown in formula 2; and R is 2 And R is 3 At least one of which is selected from the group represented by formula 2;
and is also provided withAnd R is 3 Different;
L 1 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroarylene group;
L 0 and L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroarylene group;
Z 1 selected from carbon atomsSubstituted or unsubstituted aryl groups having a number of 6 to 30, substituted or unsubstituted 5-13 membered heteroaryl groups, triphenylsilyl groups, diarylphosphonyl groups;
R 1 、R 2 、R 3 、L 0 、L 1 、L 2 and Z 1 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms optionally substituted by alkyl groups having 1 to 4 carbon atoms, 5-13 membered heteroaryl groups, trialkylsilyl groups having 3 to 12 carbon atoms;
optionally, at R 1 、R 2 、R 3 、L 0 、L 1 、L 2 And Z 1 Any two adjacent substituents are connected with each other to form a 5-10 membered aliphatic ring.
A second aspect of the present disclosure provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound of the first aspect of the present disclosure;
Optionally, the functional layer includes an electron transport layer including the organic compound;
optionally, the functional layer includes an organic light emitting layer including the organic compound.
A third aspect of the present disclosure provides an electronic device comprising the electronic component according to the second aspect of the present disclosure.
According to the technical scheme, the organic compound provided by the disclosure takes the heteroaryl containing nitrogen at two side benzene rings as a mother nucleus, at least two conjugated and connected asymmetric aromatic groups are introduced into the mother nucleus, so that the dipole moment of the compound is improved, the molecular polarity is improved, the electron mobility is improved, the aromatic groups are connected to the 2-position of the mother nucleus, the electron mobility is further improved, the triplet energy level of the compound can be regulated, and the electron mobility is improved; meanwhile, the aromatic group connected through delta bond has high rotation freedom degree, and the compound has better stereoscopicity and better film forming property. At least two groups of aromatic groups connected on the parent nucleus expand the carrier transmission area and improve the carrier migration of the compound. The compound structure is asymmetric, has obvious bipolar structure and high triplet energy level, can be used as a main material of an electron transmission layer or an organic light-emitting layer, and can remarkably improve the efficiency and the service life of an organic electroluminescent device.
Additional features and advantages of the present disclosure will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the disclosure, and are incorporated in and constitute a part of this specification, illustrate the disclosure and together with the description serve to explain, but do not limit the disclosure. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 3 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320: a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. and a second electronic device.
Detailed Description
Specific embodiments of the present disclosure are described in detail below with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating and illustrating the disclosure, are not intended to limit the disclosure.
The first aspect of the present disclosure provides an organic compound having a group represented by the following formula 1:
wherein X is 1 、X 2 、X 3 And X 4 Each independently selected from C, C (H) or N, and X 1 、X 2 、X 3 And X 4 One or two of them are N;
R 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroaryl group;
R 2 and R is 3 The substituted or unsubstituted aryl groups are the same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups or groups shown in a formula 2; and R is 2 And R is 3 At least one of which is selected from the structures shown in formula 2;
and is also provided withAnd R is 3 Different;
L 1 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5-13 membered heteroarylene group;
L 0 and L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroarylene group;
Z 1 selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups, triphenylsilyl groups and diaryl phosphono groups;
R 1 、R 2 、R 3 、L 0 、L 1 、L 2 and Z 1 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl of 1-10 carbon atoms, haloalkyl of 1-10 carbon atoms, alkoxy of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl of 6-20 carbon atoms optionally substituted by alkyl of 1-4 carbon atoms A 5-to 13-membered heteroaryl group, a trialkylsilyl group having 3 to 12 carbon atoms;
optionally, at R 1 、R 2 、R 3 、L 0 、L 1 、L 2 And Z 1 Any two adjacent substituents are connected with each other to form a 5-10 membered aliphatic ring.
In "X" of 1 1 、X 2 、X 3 And X 4 Wherein the C atom is selected from the group consisting of C atoms, which means R 3 A linked carbon atom.
In the present application, R 1 、R 2 、R 3 、L 0 、L 1 、L 2 And Z 1 The number of carbon atoms in the case of being selected from "substituted or unsubstituted (arylene) groups having a carbon number of 6 to 30" means all the number of carbon atoms. For example, if L 1 Selected from the group consisting of substituted arylene groups having 10 carbon atoms, the sum of all carbon atoms of the arylene group and substituents thereon is 10. For example, if R 1 Is 9, 9-dimethylfluorenyl, R 1 Is a substituted fluorenyl group having 15 carbon atoms, R 1 The number of ring-forming carbon atoms is 13.
The descriptions used in this disclosure that "… …" and "… …" are each independently "and" … … "are independently selected from" are interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other.
For example: in' Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluorine, chlorine" and has the meaning: the formula Q-1 represents that Q substituent groups R 'are arranged on the benzene ring, each R' can be the same or different,the options of each R' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, "hetero" means that at least 1 hetero atom such as B, N, O, S, se, si or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise.
In the present application, the term "substituted or unsubstituted" means that the functional group described later in the term may have a substituent or not. For example, "substituted or unsubstituted aryl" refers to aryl having a substituent or unsubstituted aryl. "substituted" means that it may be substituted with a substituent selected from the group consisting of: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, a 5-13 membered heteroaryl group, a trialkylsilyl group having 3 to 12 carbon atoms, and the like.
The term "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur. For example, "aryl optionally substituted with alkyl" means that alkyl may or may not be present, and the description includes both aryl substituted with alkyl and aryl not substituted with alkyl. "optionally R, attached to the same atom v2 And R is v3 Are linked to each other to form a saturated or unsaturated ring ", meaning R attached to the same atom v2 And R is v3 May be, but need not be, cyclic, the scheme including R v2 And R is v3 A scenario in which they are connected to form a ring, also including R v2 And R is v3 Scenarios that exist independently of each other.
"Ring" in the present application includes saturated rings and unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl. In the present application, alicyclic refers to a cycloalkyl group.
In the present application, "any two adjacent substituents are connected to each other to form a 5-10 membered alicyclic ring" means: two substituents attached to the same atom are linked to each other to form a 5-10 membered aliphatic ring together with the atom to which they are commonly attached, or two substituents attached to two adjacent atoms are linked to each other to form a 5-10 membered aliphatic ring together with the atom to which they are separately attached.
In the present application, "alkyl" may include a straight chain alkyl group or a branched alkyl group. Alkyl groups may have 1 to 10 carbon atoms, and in the present application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to alkyl groups that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. In some embodiments, alkyl groups contain 1 to 5 carbon atoms; in some embodiments, the alkyl groups contain 1 to 3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups having 1 to 5 carbon atoms include, but are not limited to, methyl (Me, -CH 3 ) Ethyl (Et, -CH) 2 CH 3 ) N-propyl (n-Pr, -CH) 2 CH 2 CH 3 ) Isopropyl (i-Pr, -CH (CH) 3 ) 2 ) N-butyl (n-Bu, -CH) 2 CH 2 CH 2 CH 3 ) Isobutyl (i-Bu, -CH) 2 CH(CH 3 ) 2 ) Sec-butyl (s-Bu, -CH (CH) 3 )CH 2 CH 3 ) Tert-butyl (t-Bu, -C (CH) 3 ) 3 ) A pentyl group, and the like. Furthermore, alkyl groups may be substituted or unsubstituted.
In the present application, cycloalkyl refers to a cyclic saturated hydrocarbon, comprising both monocyclic and polycyclic structures. Cycloalkyl groups may have 3-10 carbon atoms, for example, "3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3, 4, 5, 6, 7, 8, 9, 10 carbon atoms. Furthermore, cycloalkyl groups may be substituted or unsubstituted. In some embodiments, cycloalkyl is 5-10 carbon cycloalkyl, in other embodiments, cycloalkyl is 5-8 carbon cycloalkyl, examples of cycloalkyl can be, but are not limited to: 5-membered cycloalkyl (cyclopentyl), 6-membered cycloalkyl (cyclohexyl), 10-membered polycycloalkyl (such as adamantyl), and the like.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be regarded as aryl groups of the present application. Wherein the aryl does not contain B, N, O, S, se, si or P heteroatoms. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, perylene, benzofluoranthenyl,Radical, 9 dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, indenyl, and the like, without limitation thereto. In the present application, a "substituted or unsubstituted aryl group" may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms of the substituted or unsubstituted aryl group may be from 6 to 25, in other embodiments the number of carbon atoms of the substituted or unsubstituted aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms of the substituted or unsubstituted aryl group may be from 6 to 13. In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 20, 25, 26 or 30, but of course, the number of carbon atoms may be other numbers, which are not listed here.
In the present application, a substituted aryl group means that one or more hydrogen atoms in the aryl group are replaced with other groups. For example, at least one hydrogen atom is substituted with a deuterium atom, F, cl, I, -CN, hydroxy, branched alkyl, straight alkyl, haloalkyl, deuterated alkyl, trialkylsilyl, cycloalkyl, alkoxy, aryl, heteroaryl, trialkylsilyl or other groups. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to an aryl group and 18 total carbon atoms of the substituents on the aryl group. For example, 9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.
In the present application, a fluorenyl group as an aryl group may be substituted, and when two substituents are present on the fluorenyl group, optionally the two substituents may be bonded to each other to form a spiro structure, specific examples include, but are not limited to, the following structures:
in the present application, "aryl group having 6 to 20 carbon atoms optionally substituted with alkyl group having 1 to 4 carbon atoms" refers to aryl group having 6 to 20 total carbon atoms substituted with alkyl group having 1 to 4 carbon atoms or unsubstituted aryl group having 6 to 20 carbon atoms.
Aryl groups as substituents in the present application are, for example, but not limited to, phenyl, naphthyl, anthryl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl.
In the present application, heteroaryl means a monocyclic or polycyclic ring system containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms independently selected from O, N, P, si, se, B and S in the ring, and wherein at least one ring system is aromatic. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring, and either aromatic ring system containing the heteroatoms. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, isothiazolyl, oxadiazolyl, triazolyl, oxazolyl, furazayl, pyridyl, bipyridyl, phenanthridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered aryl. Pyridyl is a 6 membered heteroaryl.
In the present application, a substituted or unsubstituted heteroaryl group means a substituted or unsubstituted heteroaryl group having 5 to 13 ring atoms. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted 5-13 membered heteroaryl, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted 6-13 membered heteroaryl.
In the present application, a 5-13 membered heteroaryl group refers to a heteroaryl group having 5 to 13 ring atoms. For example, but not limited to, furyl, thienyl, imidazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, pyrazinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, dibenzothienyl, dibenzofuranyl, carbazolyl, azadibenzofuranyl, azadibenzothienyl, oxadiazolyl, and the like. Further, 5-13 membered heteroaryl groups include 5 membered heteroaryl, 6 membered heteroaryl, 7 membered heteroaryl, 8 membered heteroaryl, 9 membered heteroaryl, 10 membered heteroaryl, 11 membered heteroaryl, 12 membered heteroaryl and 13 membered heteroaryl.
In the present application, "substituted or unsubstituted 5-13 membered heteroaryl" refers to a 5-13 membered heteroaryl group having a substituent or an unsubstituted 5-13 membered heteroaryl group; the substituent on the 5-13 membered heteroaryl group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with an alkyl group having 1 to 4 carbon atoms, a 5-13 membered heteroaryl group, and a trialkylsilyl group having 3 to 12 carbon atoms.
In the present application, heteroaryl groups as substituents are, for example, but not limited to, pyridyl, pyrimidinyl, quinolinyl, dibenzothienyl, dibenzofuranyl, benzopyrimidinyl, isoquinolinyl, carbazolyl, quinolinyl, benzothiazolyl, benzoxazolyl.
In the present application, the explanation for aryl group can be applied to arylene group, the explanation for heteroaryl group can be applied to heteroarylene group as well, the explanation for alkyl group can be applied to alkylene group, and the explanation for cycloalkyl group can be applied to cycloalkylene group.
In the present application, trialkylsilyl meansWherein R is G1 、R G2 、R G3 Specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, and propyldimethylsilyl groups.
The non-positioning connection key in the present application refers to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, the naphthyl group represented by formula (f) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the carbazolyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -5).
By an off-site substituent in the context of the present application is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, the substituent R represented by the following formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by this linkage includes any one of the possible linkages represented by the formulae (Y-1) to (Y-7).
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In the present application, the haloalkyl group having 1 to 10 carbon atoms may have, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 carbon atoms, including, but not limited to, trifluoromethyl and the like.
In the present application, the alkoxy group having 1 to 10 carbon atoms may be a chain, cyclic or branched alkoxy group. The number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, including but not limited to methoxy, isopropoxy, and the like.
In the present application, the trialkylsilyl group having 3 to 12 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, including but not limited to trimethylsilyl group, etc.
In the present application, the halogen group may be selected from fluorine, chlorine, bromine, iodine.
In the present application, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be selected, for example, from the group consisting of substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracyl, phenanthryl, perylenyl, pyrenyl, and the like.
In some embodiments of the application, formula 1 is selected from structures represented by any one of formulas 1-1 to 1-6 below:
In some embodiments of the application, R 1 Selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted 6 to 13 membered heteroaryl groups.
Alternatively, R 1 The substituent of (C) is selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or 5-10 membered heteroaryl; optionally R 1 Any two adjacent substituents are connected with each other to form a 5-6 membered aliphatic ring.
In some embodiments of the application, R 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorenyl ]。
Alternatively, R 1 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, trifluoromethyl, naphthylOr a pyridyl group.
In some embodiments of the application, R 1 Selected from the group consisting of substituted or unsubstituted groups X, unsubstituted groups X being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group X has one or more substituents thereon, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, trifluoromethyl, naphthyl or pyridyl; when there are multiple substituents on the substituted group X, the substituents may be the same or different.
In some embodiments of the application, R 1 Selected from the group consisting of:
in some embodiments of the application, R 2 And R is 3 The substituted or unsubstituted aryl groups are the same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6-18 carbon atoms, substituted or unsubstituted 6-13 membered heteroaryl groups or groups shown in a formula 2; and R is 2 And R is 3 At least one of them is selected from the group represented by formula 2.
Optionally, the R 2 And R is 3 Each of the substituents is independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, 6 to 13 membered heteroaryl, haloalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms.
In some embodiments of the application, R 2 And R is 3 Identical or different and are each independently selected from hydrogen,A substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted group represented by formula a, a group represented by formula 2; and R is 2 And R is 3 At least one of which is selected from the group represented by formula 2;
alternatively, R 2 And R is 3 Each of the substituents is independently selected from deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, 6-13 membered heteroaryl, haloalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms.
In one embodiment, R 3 Is not hydrogen.
In one embodiment, R 2 Is hydrogen.
In some embodiments of the application, R 2 And R is 3 Are identical or different and are each independently selected from hydrogen, a substituted or unsubstituted group Y or a group of formula 2, and R 2 And R is 3 At least one of which is selected from the group represented by formula 2; the unsubstituted group Y is selected from the group consisting of:
wherein,represents a chemical bond; the substituted group Y has one or more substituents;
alternatively, the substituents on the group Y are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl, pyridinyl, trifluoromethyl, trimethylsilyl, quinazolinyl, pyrimidinyl, dibenzothienyl, dibenzofuranyl, or benzoxazolyl; when there are multiple substituents on the substituted group Y, the substituents may be the same or different.
Alternatively, the substituents on the group Y are each independently selected from deuterium, fluorine, cyano, alkyl of 1 to 5 carbon atoms, cycloalkyl of 5 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, 6 to 13 membered heteroaryl, trifluoromethyl or trimethylsilyl.
In some embodiments of the application, R 2 And R is 3 Identical or different and are each independently selected from the group consisting of hydrogen, a group of formula 2 or:
in some embodiments of the application, R 2 And R is 3 Are not identical.
In some embodiments of the application, L 1 Selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 26 carbon atoms, and a substituted or unsubstituted 5-to 13-membered heteroarylene group.
Optionally, the L 1 Each of the substituents in (a) is independently selected from deuterium, a halogen group, cyano, alkyl having 1 to 5 carbon atoms, cycloalkyl having 3 to 5 carbon atoms, aryl having 6 to 15 carbon atoms optionally substituted with alkyl having 1 to 4 carbon atoms, and 6 to 13 membered heteroaryl.
In some embodiments of the application, L 1 Selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzoyleneThienyl, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triazinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted benzothiazolylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted group of formula B;
Alternatively, L 1 Each of the substituents of (2) is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, naphthyl, phenyl, biphenyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl.
In some embodiments of the application, L 1 Selected from substituted or unsubstituted radicals V 1 Unsubstituted group V 1 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 1 Having one or more substituents thereon, each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, cyclopentyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl; when the substituted group V 1 When there are a plurality of substituents, the substituents may be the same or different.
In some embodiments of the application, L 1 Selected from the group consisting of:
in some embodiments of the application, L 0 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted 5 to 13 membered heteroarylene group.
Alternatively, L 0 And L 2 The substituents in (2) are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-5 carbon atoms, cycloalkyl group having 5-10 carbon atoms, and aryl group having 6-12 carbon atoms.
In some embodiments of the application, L 0 Selected from single bonds, substituted or unsubstituted groups V 2 Unsubstituted group V 2 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 2 Having one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, cyclopentyl, phenyl or naphthyl; when the substituted group V 2 When there are a plurality of substituents, the substituents may be the same or different.
In some embodiments of the application, L 0 Selected from the group consisting of single bonds or:
in some embodiments of the application, L 2 Selected from single bonds, substituted or unsubstituted groups V 3 Unsubstituted group V 3 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 3 Having one or more substituents thereon, each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, cyclopentyl, biphenyl, phenyl, naphthyl; when the substituted group V 3 When there are a plurality of substituents, the substituents may be the same or different.
In some embodiments of the application, L 2 Selected from the group consisting of single bonds or:
in some embodiments of the application, Z 1 Selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups, diaryl phosphono groups, and triphenyl silicon groups.
Optionally, the Z 1 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-5 carbon atoms, cycloalkyl group having 5-10 carbon atoms, aryl group having 6-12 carbon atoms.
In some embodiments of the application, Z 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstitutedOr unsubstituted benzothienyl, diphenylphosphono, substituted or unsubstituted quinolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorenyl ] ]Substituted or unsubstituted spiro [ cyclohexane-1, 9' -fluorenyl ]]A substituted or unsubstituted group of formula C;
optionally, the Z 1 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, phenyl, naphthyl.
In some embodiments of the application, Z 1 Selected from the group consisting of substituted or unsubstituted groups W, unsubstituted groups W being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group W has one or more substituents, and each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl and phenyl; when there are a plurality of substituents on the substituted group W, the substituents may be the same or different.
In some embodiments of the application, Z 1 Selected from the group consisting of:
in one embodiment of the present application, the group of formula 2 is selected from the group consisting of:
in one embodiment of the application, the organic compound is selected from the group consisting of:
a second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound according to the first aspect of the present application.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be, for example, a red organic electroluminescent device, a green organic electroluminescent device, or a blue organic electroluminescent device.
Optionally, the organic electroluminescent device is a red organic electroluminescent device or a blue organic electroluminescent device.
For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in the first aspect of the present application.
In one embodiment of the present application, the functional layer 300 includes an electron transport layer 340, and the electron transport layer 340 includes the organic compound.
In one embodiment of the present application, the functional layer 300 includes an organic light emitting layer 330, and the organic light emitting layer 330 includes the organic compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322.
In one embodiment, the anode 100 comprises the following anode materials, preferably to facilitate cavitationA hole is implanted into the functional layer of a material having a large work function. The anode material specifically comprises: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides such as ZnO: al and SnO 2 : sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, and the first hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited in the present application. Specifically, the first hole transport layer 321 is composed of a compound NPBAPF or Spiro-TPD.
In one embodiment, the second hole transport layer 322 may include one or more hole transport materials, and the second hole transport layer material may be selected from carbazole multimers or other types of compounds, which are not particularly limited in the present application. In one embodiment, the second hole transport layer 322 is composed of the compound TTP or α -NPD.
In the present application, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials further including a material selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 contains the organic compound of the present application, and for example, may be composed of the organic compound of the present application and LiQ together. In another embodiment of the present application, electron transport layer 340 is comprised of both BTB and LiQ.
In one embodiment, the organic light emitting layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 may be an organic compound of the present application or may be composed of an organic compound of the present application together with other light emitting host materials, such as a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, to which the present application is not limited in particular. In a specific embodiment, the host material of the organic light emitting layer 330 comprises the compound of the present application. Alternatively, the host material is composed of EFIN or the organic compound of the present application.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. In one embodiment, the guest material of the organic light emitting layer 330 is PCAN or Ir (piq) 2 (acac)。
Optionally, the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. In particular, specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; multilayer materials such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.
In the present application, as shown in fig. 1, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. For example, the hole injection layer 310 may be composed of PPDN or m-MTDATA.
In one embodiment, as shown in fig. 1, an electron injection layer 350 may also be provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may include LiQ.
In one embodiment, the electronic component is a photoelectric conversion device. As shown in fig. 2, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the electron transport layer includes the nitrogen-containing compound of the present application.
A third aspect of the present disclosure provides an electronic device comprising the electronic element provided in the second aspect of the present disclosure. Since the electronic device has any one of the electronic components described in the above-mentioned electronic component embodiments, the present application has the same beneficial effects, and will not be described herein.
As shown in fig. 3, one embodiment of the present application provides a first electronic device 400. The electronic device comprises the organic electroluminescent device. The first electronic device 400 may be a display device, a lighting device, an optical communication device, or other type of electronic device, and may include, for example, but not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, a light module, a CCD camera, or other type of electronic device.
The present disclosure is further illustrated by the following examples, but is not so limited.
The method of synthesizing the organic compound provided by the present application is not particularly limited, and a person skilled in the art can determine a suitable synthesis method from the method of preparing the organic compound according to the present application in combination with the method of preparing provided in the examples section. All organic compounds provided by the present application can be obtained according to these exemplary preparation methods by a person skilled in the art, and all specific preparation methods for preparing the organic compounds are not described in detail herein, and the person skilled in the art should not be construed as limiting the present application.
In the synthesis examples described below, all temperatures are in degrees celsius unless otherwise indicated. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company and some intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials, and were used without further purification unless otherwise stated. The rest of conventional reagents are purchased from Nanjing Kang Man forestry chemical industry Co., ltd, qingdao Tenglong chemical reagent Co., qingdao ocean chemical works, etc.
In purification, the chromatographic column is a silica gel column, and silica gel (80-120 mesh) is purchased from Qingdao ocean chemical plant.
In each synthesis example, the measurement conditions for low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage HPLC-M (column type: zorbax SB-C18, 2.1X130 mm,3.5 μm, 6min, flow rate 0.6mL/min. Mobile phase: 5% -95% (acetonitrile with 0.1% formic acid) in water with 0.1% formic acid) was detected by electrospray ionization (ESI) at 210nm/254nm with UV.
Nuclear magnetic resonance hydrogen spectrum: bruker 400MHz nuclear magnetic instrument, under room temperature condition, CDCl 3 Or CD (compact disc) 2 Cl 2 TMS (0 ppm) was used as a reference standard for solvents (in ppm).
Synthesis of intermediates of the following Structure
Synthesis of intermediate I
(1) Nitrogen (0.100L/min) is introduced into a sealed reaction vessel for replacement for 2min, raw material I-1 (100 mmol,31.6 g), raw material I-2 (105 mmol), triethylamine (200 mmol,28 mL), palladium acetate (1 mmol) and 100mL toluene are heated to 100-105 ℃ for reaction for 12h, 50mL of water is added, the liquid is separated, and the aqueous phase is extracted for 1 time by 50mL of toluene. The combined organic phases were washed 2 times with water, the organic phases were dried over 5g of anhydrous sodium sulfate, filtered, the organic phases were concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa.) until no droplets were present, 50mL of ethanol was added with stirring, and filtration was carried out to give 70.3mmol of intermediate I-3 in 70.3% yield.
(2) After nitrogen is introduced into a three-neck flask with mechanical stirring, a thermometer and a condenser tube for 10min (2000 mL/min), intermediate I-3 (60 mmol), raw materials 1-4 (66 mmol), potassium carbonate (90 mmol), 80.0mL of methanol and 40.0mL of acetonitrile are added, stirring is started, the temperature is raised to 40-45 ℃, palladium acetate (1.2 mmol) is added, the temperature is continuously raised to 60-65 ℃ for reaction for 3h, the reaction liquid is cooled to 25 ℃, then the reaction liquid is filtered, the solid is leached by ethanol, 50mmol of intermediate I-5 is obtained, and the yield is 83.3%.
(3) Nitrogen (0.100L/min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer and a condenser for 15min of displacement, and then intermediate I-5 (40 mmol), triphenylphosphine rhodium chloride (0.4 mmol) and 60mL of 1, 4-dioxane were added in sequence. Heating to 85-90 ℃ for reaction for 5h, adding 120mL of water, filtering, pulping a filter cake with 50mL of ethanol for 1 time, and filtering to obtain 7.33g of intermediate I with the yield of 85%.
Intermediate II-intermediate V was synthesized with reference to the synthesis method of intermediate I, except that the raw material Y1 in Table 1 below was used in place of the raw material I-4 in the above-mentioned step (2).
TABLE 1
Synthesis example 1 Synthesis of Compound 2
(1) A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, then, raw material 2a (50 mmol,12.46 g), raw material 2b (CAS: 1100754-73-1,55mmol,17.83 g), potassium carbonate (100 mmol,13.8 g), tetrabutylammonium bromide (5 mmol,1.61 g), 120mL toluene, 40.0mL ethanol and 40.0mL water were sequentially added, stirring was started, the temperature was raised to 40-45℃and tetrakis triphenylphosphine palladium (5 mmol,5.78 g) was added, the temperature was continuously raised to 60-65℃for reaction for 8h, 50mL of water was added, the mixture was separated, and the aqueous phase was extracted 1 time with 50mL toluene. The combined organic phases were washed 2 times with water, dried over 5g of anhydrous sodium sulfate, filtered, and concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa.) to 30mL for recrystallization to afford intermediate 2c (30 mmol,14.8 g) in 60% yield.
(2) A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, then intermediate 2c (20 mmol,9.86 g), raw material 2d (22 mmol,4.36 g), potassium carbonate (40 mmol,5.52 g), tetrabutylammonium bromide (2 mmol,0.65 g), 60mL toluene, 20.0mL ethanol and 20.0mL water were added in this order, stirring was started, the temperature was raised to 40-45 ℃, dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (1 mmol,0.71 g) was added, the temperature was continuously raised to 60-65℃for reaction for 1h, 20mL of water was added, the mixture was separated, and the aqueous phase was extracted 1 time with 20mL toluene. The combined organic phases were washed with water for 2 times, the organic phases were dried over 2g of anhydrous sodium sulfate, filtered, and the organic phases were concentrated 50-60 ℃ and-0.09-0.08 Mpa) until no liquid flows out, 10mL of ethanol is added, and the mixture is filtered to obtain 10.02g of compound 2 with the yield of 82 percent. LC-MS (ESI, pos.ion) m/z=611.2 [ m+h ]] + 。 1 H NMR(CDCl 3 ,400MHz):9.03-8.99(d,1H),8.79-8.73(m,4H),8.55-8.52(d,1H),8.47(s,2H),8.24-8.21(d,1H)，8.15-8.11(m,2H),8.06(s,1H),7.88-7.79(m,7H),7.69-7.66(d,1H),7.53-7.44(m,8H),7.31-7.29(m,2H).
Synthesis examples 2 to 28
The compounds in table 2 were synthesized with reference to the synthesis of compound 2, except that raw material Y2 was used instead of raw material 2b, and raw material Y3 was used instead of raw material 2d, and the numbers, structures, yields and mass spectrum data are shown in table 2.
TABLE 2
Synthesis example 29 Synthesis of Compound 114
(1) A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, then intermediate I (30 mmol,6.47 g), raw material 114a (30 mmol,9.73 g), potassium carbonate (60 mmol,8.28 g), tetrabutylammonium bromide (6 mmol,1.93 g), 100mL toluene, 20.0mL ethanol and 20.0mL water were added in this order, stirring was started, the temperature was raised to 40-45 ℃, dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.3 mmol,0.22 g) was added, the temperature was continuously raised to 60-65℃for reaction for 1h, 30mL of water was added, the mixture was separated, and the aqueous phase was extracted 1 time with 45mL toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phases concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa.) until no droplets were present, and filtered through the addition of 25mL of ethanol to give intermediate 114b (28.6 mmol,12.53 g) in 95.3% yield.
(2) Introducing nitrogen (0.100L/min) into a three-port bottle with a mechanical stirring thermometer and a spherical condenser tube for 15min replacement, sequentially adding an intermediate 114b (20 mmol,9.19 g) and tetrahydrofuran 60mL, starting stirring, cooling to-65 ℃ to-60 ℃, dropwise adding LDA (24 mmol,12 mL), keeping the temperature for 1h after dropwise adding, dropwise adding a solution of a raw material 114c (24 mmol,6.80 g) and 20mL tetrahydrofuran, keeping the temperature for 1h after dropwise adding, adding 50mL of water, extracting with dichloromethane 50mL, extracting the aqueous phase with 30mL of dichloromethane, combining the organic phases, washing 2 times with water, drying the organic phases with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phases (40-45 ℃ C., -0.06-0.05 Mpa) until no liquid flows out, adding 10mL of petroleum ether, filtering to obtain 9.6g of a compound 114, and obtaining the compound with the yield of 72.5%, LC-MS (ESI, pos.m/z=2 [ M+H 662 ]] + 。
Synthesis examples 30 to 63
The compounds in Table 3 were synthesized with reference to the synthesis method of compound 114, except that raw material Y4 was used in place of raw material 114a, and raw material Y5 was used in place of raw material 114c, and the numbers, structures, yields and mass spectrum data of the synthesized compounds are shown in Table 3.
TABLE 3 Table 3
The following intermediates were synthesized by the synthetic method of reference compound 2, except that raw material Y6 was used instead of raw material 2a, raw material Y7 was used instead of 2d, and the numbers, structures, and yields are listed in table 4.
TABLE 4 Table 4
Synthesis example 64 Synthesis of Compound 219
(1) To a three-necked flask equipped with a mechanical stirrer and a thermometer, nitrogen (0.100L/min) was introduced for 15min, 219m (20 mmol,8.17 g) of intermediate and 60mL of dichloroethane were sequentially added, stirring was started, the temperature was lowered to-5℃to 0℃and bromine (21 mmol,3.34 g) was added dropwise, the dropwise was continued to keep warm for 5 hours, 50mL of water was added, the liquid was separated, the aqueous phase was extracted with 30mL of dichloroethane again, the organic phase was combined and washed with water for 2 times, the organic phase was dried over 2g of anhydrous sodium sulfate, filtration was carried out, the organic phase was concentrated (40℃to 45℃and-0.06 to-0.05 MPa) to dryness, and the obtained product was concentrated with ethyl acetate: petroleum ether=1 mL:18mL column chromatography gives intermediate 219a (10 mmol,4.87 g) in 50% yield.
(2) Introducing N into a three-mouth bottle with mechanical stirring, thermometer and condenser tube 2 (0.100L/min) for 15min, intermediate 219a (10 mmol,4.87 g), raw material 219b (10.5 mmol,2.08 g), potassium carbonate (20 mmol,2.76 g), tetrabutylammonium bromide (1 mmol,0.33 g), 30mL toluene, 15mL ethanol, 10.0mL water were added in this order, stirred and warmed to 40-45 ℃, dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.2 mmol,0.14 g) was added, reacted at 60-65℃for 2h, 10mL water was added, the mixture was separated, and the aqueous phase was extracted with 10mL toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phases were concentrated (50-60 ℃, -0.09 to-0.08 Mpa) to dryness, 15mL of ethanol was added, and filtered to give compound 219 (5.2 g, yield 93%).
LC-MS(ESI,pos.ion)m/z＝561.2[M+H] + ；
1 HNMR(CDCl 3 ,400MHz):8.83-8.79(m,2H),8.37-8.32(m,4H),8.01(s,1H),7.79-7.73(m,6H),7.57(s,1H)，7.52-7.47(m,5H),7.43-7.35(m,7H),7.31-7.29(d,1H),7.19-7.16(d,1H).
Synthesis examples 65 to 74
The following compounds were synthesized by the synthetic method of reference compound 219, except that starting material Y8 was used instead of intermediate 219m, starting material Y9 was used instead of 219b, and the compound numbers, structures, yields and mass spectrum data are shown in table 5.
TABLE 5
Synthesis example 75 Synthesis of Compound 293
(1) A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, then intermediate I (30 mmol,6.45 g), phenylboronic acid (33 mmol,4.03 g), potassium carbonate (60 mmol,8.28 g), tetrabutylammonium bromide (3 mmol), 100mL toluene, 20.0mL ethanol and 20.0mL water were added in this order, stirring was started, the temperature was raised to 40-45 ℃, dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.3 mmol) was added, the temperature was continuously raised to 60-65 ℃ for reaction for 1h, 20mL of water was added, the mixture was separated, and the aqueous phase was extracted 1 time with 50mL toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phases concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa.) until no droplets were present, and filtered through the addition of 20mL of ethanol to give 7.35g of intermediate 293b in 95.3% yield.
(2) Nitrogen (0.100L/min) is introduced into a three-port bottle provided with a mechanical stirring and thermometer for 15min replacement, intermediate 293b (20 mmol,5.14 g) and dichloroethane (60 mL) are sequentially added, stirring is started, the temperature is reduced to-5 ℃ to 0 ℃, bromine (21 mmol) is added dropwise, the temperature is kept for 8h after the dropwise addition, 40mL of water is added, the liquid is separated, the aqueous phase is extracted with 30mL of dichloroethane again, the organic phase is combined and washed with water for 2 times, the organic phase is dried with 2g of anhydrous sodium sulfate, filtered, the organic phase is concentrated (40 ℃ to 45 ℃ and-0.06 to-0.05 Mpa) until dry, the obtained solid is recrystallized with toluene, and 2.68g of intermediate 293c is obtained, and the yield is 40%.
(3) A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, then intermediate 293c (10 mmol,3.35 g), raw material 293d (11 mmol,3.16 g), potassium carbonate (20 mmol,2.76 g), tetrabutylammonium bromide (1 mmol), 30mL of toluene, 10.0mL of ethanol and 10.0mL of water were added in this order, stirring was started, the temperature was raised to 40℃to 45℃and dichlorodi-tert-butyl- (4-dimethylaminophenyl) phosphine palladium (0.1 mmol) was added, the temperature was continued to be raised to 60℃to 65℃for 2h, water was added for 10mL, the mixture was separated, and the aqueous phase was extracted 1 time with 10mL of toluene. The combined organic phases were washed 2 times with water, dried over 2g of anhydrous sodium sulfate, filtered, the organic phases concentrated (50 ℃ C. -60 ℃ C., -0.09 to-0.08 MPa) until no droplets were present, 15mL of ethanol was added, and filtered to give 4.70g of intermediate 293e in 94.2% yield.
(4) Introducing nitrogen (0.100L/min) into a three-port bottle with a mechanical stirring thermometer and a spherical condenser tube for 15min replacement, sequentially adding an intermediate 293e (5 mmol,2.49 g) and 30mL of tetrahydrofuran, starting stirring, cooling to-65 to-60 ℃, dropwise adding LDA (13 mmol,6.5 mL), continuously preserving heat for 1h after dropwise adding, dropwise adding a solution of a raw material 293f (12 mmol,3.02 g) and 10mL of tetrahydrofuran, continuously preserving heat for 1h after dropwise adding, adding 30mL of water, extracting with dichloromethane 20mL, extracting an aqueous phase with 20mL of dichloromethane, combining an organic phase, washing 2 times with water, drying the organic phase with 2g of anhydrous sodium sulfate, filtering, concentrating the organic phase (40-45 ℃ C., -0.06-0.05 Mpa) until no liquid flows out, adding 8mL of petroleum ether, filtering to obtain a compound 293 (2.33 g, yield 69.8%), LC-MS (ESI, pos.m/z=669.2 [ M+H ] ] + 。
The following compounds were synthesized by the synthetic method of reference compound 293, except that raw material Y10 was used instead of phenylboronic acid, raw material Y11 was used instead of 293d, and raw material Y12 was used instead of 293f, and the numbers, structures, yields and mass spectrum data are shown in table 6.
TABLE 6
Synthesis examples 90 to 97
Referring to the synthesis of compound 2, starting material Y13 was used in place of starting material 2b, starting material Y14 was used in place of starting material 2d, and the compounds of Table 7 were synthesized with the numbers, structures, yields and mass spectrometry data set forth in Table 7.
TABLE 7
Synthesis examples 96 to 101
Referring to the synthesis of compound 114, the compounds in table 8 were synthesized using intermediate II instead of intermediate I, starting material V instead of starting material 114a, starting material VI instead of starting material 114c, and the compound numbers, structures, yields and mass spectrometry data are listed in table 8.
TABLE 8
Synthesis examples 102 to 113
The following table compounds were synthesized with reference to the complete synthesis of compound 219. Wherein first, referring to the synthesis of compound 2, starting material 2a was replaced with intermediate III or intermediate V, starting material Y15 was replaced with 2b, starting material Y16 was replaced with 2d, to prepare intermediate xxxm (xxx represents compound number), and referring to the last two steps of the preparation of compound 219, starting material Y17 was replaced with 219b, the following compounds were synthesized, and the numbers, structures, yields and mass spectrometry data are listed in table 9.
TABLE 9
Example preparation and property evaluation of blue organic electroluminescent device
Example 1
The anode was prepared by the following procedure: the ITO thickness is equal toThe ITO substrate of (C) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a photolithography step was used to prepare an experimental substrate having cathode, anode and insulating layer patterns, and ultraviolet ozone and O were used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
PPDN (CAS: 215611-93-1) was vacuum evaporated onto a test substrate (anode) to form a film of thicknessIs deposited on the Hole Injection Layer (HIL) by vacuum evaporation to form NPBAPF (CAS: 510775-24-3) having a thickness of +.>A first Hole Transport Layer (HTL).
Evaporating TTP (CAS: 80223-29-6) on the first Hole Transport Layer (HTL) to form a film having a thickness ofIs a second hole transport layer (EBL).
PCAN (CAS: 1261580-75-9) was simultaneously doped with EFIN (CAS: 1705571-72-7) as a main body at a film thickness ratio of 97:3 to form a film having a thickness ofAn organic light emitting layer (EML).
The compound 2 and LiQ are mixed in a weight ratio of 1:1 and can be formed by an evaporation process A thick Electron Transport Layer (ETL). Subsequently, liQ is evaporated on the electron transport layer to form a film having a thickness +.>Then, magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the Electron Injection Layer (EIL) to form a film with a thickness ofIs provided.
In addition, the thickness of the vapor deposited on the cathode isAnd forming a capping layer (CPL), thereby completing the manufacture of the blue organic electroluminescent device.
Examples 2 to 84
In examples 2 to 84, an organic electroluminescent device was produced in the same manner as in example 1, except that the compounds in table 11 were used in place of the compound 2, respectively.
Comparative examples 1 to 3
In comparative examples 1 to 3, an organic electroluminescent device was prepared in the same manner as in example 1, except that compound a, compound B, and compound C were used instead of compound 2, respectively, wherein the structural formulas of compound a, compound B, and compound C are shown in table 10 below:
table 10:
the organic electroluminescent devices obtained in examples 1 to 84 and comparative examples 1 to 3 were subjected to a temperature of 15mA/cm 2 Under the condition of testing the service life of a T95 device, the data working voltage, the efficiency and the color coordinates are that the constant current density is 10mA/cm 2 The test was performed as follows, and the results are shown in table 11.
TABLE 11
As can be seen from the data in Table 11, the organic electroluminescent devices prepared in examples 1 to 84 using the compound of the present application as an electron transport material have a current efficiency (Cd/A) improved by at least 10.3% and a lifetime improved by at least 15% while ensuring a lower operating voltage, as compared with the devices prepared in comparative examples 1 to 3 using the compound A, B, C, respectively.
Example 85 Red organic electroluminescent device
The anode was prepared by the following procedure: will beThickness is as followsThe ITO substrate (manufactured by Corning) was cut into a size of 40 mm. Times.40 mm. Times.0.7 mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by a photolithography step, and an ultraviolet ozone and O were used 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum. And the surface of the ITO substrate can be cleaned by adopting an organic solvent so as to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating m-MTDATA (CAS: 124729-98-2) on an experimental substrate (anode) to form a thickness of thicknessIs deposited on the Hole Injection Layer (HIL), and the Spiro-TPD (CAS: 1033035-83-4) is formed to a thickness of +. >Is provided.
Vacuum deposition of alpha-NPD (CAS: 495416-60-9) on the hole transport layer to form a film of thicknessIs provided.
Compound 277: ir (piq) 2 (acac) at 97%: co-evaporation was performed at a film thickness ratio of 3% to form a film having a thickness ofRed light organic light emitting layer (R-EML).
BTB (CAS: 266349-83-1) and LiQ were mixed in a weight ratio of 1:1 and evaporated to formA thick Electron Transport Layer (ETL), liQ is evaporated on the electron transport layer to form a thickness +.>Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) are mixed at 1:9, and vacuum evaporating on the electron injection layer to form a film with a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device, the structure of which is shown below. />
Examples 86 to 113
In examples 86 to 113, an organic electroluminescent device was produced in the same manner as in example 85, except that the compounds shown in Table 12 were used in place of the compound 277, respectively.
Comparative examples 4 to 7
In comparative examples 4 to 7, an organic electroluminescent device was prepared by the same method as in example 85, except that compound D, compound E, compound F, and compound G were used instead of compound 277, respectively, wherein the structural formulae of compound D, compound E, compound F, and compound G were as follows:
。
The organic electroluminescent devices obtained in examples 85 to 113 and comparative examples 4 to 7 were subjected to a temperature of 15mA/cm 2 Under the condition of testing the service life of a T95 device, the data working voltage, the efficiency and the color coordinates are that the constant current density is 10mA/cm 2 The test was performed as follows, and the results are shown in table 12.
Table 12
From the data in Table 12, it is understood that the organic electroluminescent devices prepared in examples 85 to 113 using the compound of the present application as the host material for the organic light emitting layer have a current efficiency (Cd/A) improved by at least 11% and a lifetime improved by at least 19% while securing a lower operating voltage, as compared with the devices prepared in comparative examples 4 to 7 using the compound D, E, F, G, respectively.
The foregoing detailed description of some representative embodiments of the present disclosure has been given with reference to the accompanying drawings, but the present disclosure is not limited to the specific details of the foregoing embodiments, and many simple modifications may be made to the technical solutions of the present disclosure within the scope of the technical concept of the present disclosure, and all the simple modifications belong to the protection scope of the present disclosure.
Claims (24)
1. An organic compound, characterized in that the organic compound has a structure represented by the following formula 1:
wherein X is 1 Selected from N;
X 3 Selected from C, C (H) or N;
X 2 and X 4 Selected from C (H) or C;
R 1 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 13 membered heteroaryl group;
R 2 selected from hydrogen, number of carbon atoms6 to 30 substituted or unsubstituted aryl or a group of formula 2;
R 3 selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted 5-13 membered heteroaryl group, or a group represented by formula 2;
and R is 2 And R is 3 At least one of which is selected from the structures shown in formula 2;
and is also provided withAnd R is 3 Different;
L 1 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted 5-13 membered heteroarylene group;
L 2 selected from single bond, substituted or unsubstituted arylene group with 6-30 carbon atoms, and substituted or unsubstituted 5-13 membered heteroarylene group;
L 0 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms selected from a single bond;
Z 1 selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups, triphenylsilyl groups and diphenylphosphono groups;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms or phenyl group;
R 3 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, phenyl or quinazolinyl;
L 0 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms or phenyl group;
L 1 、L 2 the substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 10 carbon atoms or phenyl group;
Z 1 the substituents in (a) are the same or different and are each independently selected from deuterium, halogenA group, a cyano group, an alkyl group having 1 to 10 carbon atoms, or a phenyl group.
2. The organic compound according to claim 1, wherein the organic compound has a structure represented by the following formula 1-1 or formula 1-3:
。
3. the organic compound according to claim 1, wherein R 1 Selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted 6 to 13 membered heteroaryl groups.
4. An organic compound according to claim 3, wherein R 1 The substituent of (C) is selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, and phenyl.
5. The organic compound according to claim 1, wherein R 1 Selected from the group consisting of substituted or unsubstituted groups X, unsubstituted groups X being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group X has one or more substituents, and each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary butyl and phenyl; when there are multiple substituents on the substituted group X, the substituents may be the same or different.
6. The organic compound according to claim 1, wherein the R 2 Selected from hydrogen, substituted or unsubstituted aryl with 6-18 carbon atoms or a group shown in formula 2;
R 3 selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, unsubstituted 6 to 13 membered heteroaryl groups, or groups represented by formula 2.
7. The organic compound according to claim 6, wherein the R 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, phenyl;
the R is 3 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, phenyl group or quinazolinyl group.
8. The organic compound according to claim 1, wherein the R 2 Selected from hydrogen, a substituted or unsubstituted group Y or a group represented by formula 2; the unsubstituted group Y is selected from the group consisting of:
wherein,represents a chemical bond; the substituted group Y has one or more substituents;
the substituent groups on the group Y are independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms and phenyl;
R 3 selected from substituted or unsubstituted radicals Y 1 Unsubstituted group Y 2 Or a group of formula 2, and R 2 And R is 3 At least one of which is selected from the group represented by formula 2; wherein the unsubstituted radical Y 1 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group Y 1 Having one or more substituents thereon;
said group Y 1 The substituents on the substrate are independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, phenyl, quinazolinyl and trifluoromethyl;
unsubstituted group Y 2 Selected from the group consisting of:
9. an organic compound according to claim 8, wherein the substituents on the group Y are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the substituted group Y has a plurality of substituents, the substituents are the same or different;
said group Y 1 The substituents on each are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, quinazolinyl, trifluoromethyl; when the substituted group Y 1 When there are a plurality of substituents, the substituents may be the same or different.
10. The organic compound according to claim 1, wherein the L 1 Selected from substituted or unsubstituted radicals V 1 Unsubstituted group V 1 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 1 Having one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the substituted group V 1 When there are a plurality of substituents, the substituents may be the same or different.
11. The organic compound according to claim 1, wherein the L 0 A substituted or unsubstituted arylene group having 6 to 20 carbon atoms selected from a single bond;
L 2 selected from single bond, substituted or unsubstituted arylene group with 6-20 carbon atoms, and substituted or unsubstituted 5-13 membered heteroarylene group.
12. The organic compound according to claim 11, wherein the L 0 And L 2 The substituents in (a) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and phenyl.
13. The organic compound according to claim 1, wherein the L 0 Selected from single bonds, substituted or unsubstituted groups V 2 Unsubstituted group V 2 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 2 Having one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the substituted group V 2 When there are a plurality of substituents, the substituents may be the same or different.
14. The organic compound according to claim 1, wherein the L 2 Selected from single bonds, substituted or unsubstituted groups V 3 Unsubstituted group V 3 Selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V 3 Having one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the substituted group V 3 When there are a plurality of substituents, the substituents may be the same or different.
15. The organic compound according to claim 1, wherein the Z 1 Selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted 5-13 membered heteroaryl groups, diphenylphosphono groups, and triphenylsilyl groups.
16. The organic compound according to claim 15, wherein Z 1 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-5 carbon atoms, phenyl group.
17. The organic compound according to claim 1, wherein the Z 1 Selected from the group consisting ofA substituted or unsubstituted group W selected from the group consisting of:
wherein,represents a chemical bond; the substituted group W has one or more substituents, and each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl; when there are a plurality of substituents on the substituted group W, the substituents may be the same or different.
18. An organic compound, characterized in that the organic compound is selected from the group consisting of:
19. an electronic component, characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1 to 18.
20. The electronic component of claim 19, wherein the functional layer comprises an electron transport layer comprising the organic compound.
21. The electronic component of claim 19, wherein the functional layer comprises an organic light-emitting layer comprising the organic compound.
22. The electronic component of any of claims 19-21, wherein the electronic component is an organic electroluminescent device.
23. The electronic component of claim 22, wherein the organic electroluminescent device is a blue organic electroluminescent device or a red organic electroluminescent device.
24. An electronic device comprising the electronic component of any one of claims 19-23.
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